The 50th Annual Skipjack Races

Labor Day weekend is most often spent by Marylanders as a last chance to go to the beach or have the family over for some crabs. What most of us don’t know is that an old sailing tradition in our state is held on Labor day down on Deal Island, far south on our eastern shore. The Annual Skipjack Races, now in its 50th year sponsored by the Deal Island-Chance Lions club, offers a chance for the last remaining Skipjack captains to test their sailing skills as well as give welcome visitors the opportunity to ride along on a historic Chesapeake Bay oystering vessel.

I decided to make the trek from Baltimore to Chance harbor to photograph the historic event with the hopes that I could do so from deck of one specific boat, the ‘City of Crisfield’. This Skipjack is owned and operated by the only captain that has been in every race since its conception, 88 year old Arthur “Daddy Art” Daniels, Jr. Daddy Art has won nine races over the years including the one last year with a crew that he describes as “a family affair”, which manned by his sons and grandsons.

This year’s event was comprised of 11 Skipjacks, just about all that is left of this fast vanishing sailing fleet that once numbered over 1000 in the late 1800’s. Few of which like the ‘Thomas Clyde’ continue dredging oysters to this day. Other vessels are owned and operated by educational foundations like the ‘Sigsbee’, sailed by Living Classrooms, and this years race winner the ‘Martha Lewis’ which is part of the Chesapeake Heritage Conservancy in Havre de Grace.